Potassium Cyanide → 6-((2,2-Diphenylethyl)amino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carbonitrile

HRID 1293034Notes

Reaction equation

HRID 1293034 reaction equation
[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17](S(C)(=O)=O)[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:35]#[N:36].[K+]>CN(C)C=O.O>[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:35]#[N:36])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 21978255N-(2,2-Diphenylethyl)-2-(methylsulphonyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

Product 1

HCID 101593916-((2,2-Diphenylethyl)amino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carbonitrileYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of N-(2,2-diphenylethyl)-2-(methylsulfonyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (Preparation 22) (20.1 g, 42.1 mmol) in dry N,N-dimethylformamide (100 ml) was treated with potassium cyanide (5.5 g, 84.6 mmol) and the mixture was heated at 120° C. for 24 hours under a nitrogen atmosphere. The mixture was cooled to room temperature and diluted with water (1000 ml) and stirring was continued for a further 1 hour. The resultant solid was filtered off and washed several times with water. The solid was then dissolved in dichloromethane and the solution was washed with water, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The residue was azeotroped with diethyl ether (twice) to afford the title compound as an oil (17 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe resultant solid was filtered off
  3. washwashed several times with water
  4. dissolutionThe solid was then dissolved in dichloromethane
  5. washthe solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was azeotroped with diethyl ether (twice)

Sources & evidence

ORD record
ord-8f16df4103ed433ab0b5be8c7fdc750b
Source dataset
uspto-grants-2007_07
Patent number
US07238676B2

Reaction notes

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